Max your upgrade chances...


Boosting the probability of getting upgraded
Now you already know what type of upgrade you are trying to get (free/paid), you know to request it at booking, and to get on the airport list if you didn’t get it by the time you reached to the airport. FROM MY EXPERIENCE THERE ARE A NUMBER OF THINGS YOU CAN DO THAT WILL MAX YOUR CHANCES OF GETTING UPGRADED. If you have had a different or similar experiences or some other advice please add you own thoughts below

Timing and routes I (e.g. 06:30 vs. 07:00)
on some routes such as NYC-Chicago (LGA-ORD) I have found that people tend to book the flight on the hour and are not aware that at some hours there is also a flight on the half hour (e.g. 06:30, 05:30). I have taken many 07:00 am flights and requested an upgrade a couple of days before the flight or at the airport without much success, I then started taking the 06:30 flight and got upgraded on the same days about 50%-60% of the time. MUCH BETTER!

Timing and routes II (Mon-Thu)
Typically Monday morning and Thursday night are full of business travelers with high tier status – during these days it is harder to get upgraded. Traveling Monday afternoon/night or Wednesday for example greatly increases your chances of upgrades

Early bird gets the upgrade
There are two factors that will determine your chances of getting an upgrade, the time you get put on the list and your status. Higher status gets preference, but timing determines preference within a status group